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This page looks at the polymerisation of alkenes to produce polymers like poly(ethene)
(usually known as polythene, and sometimes as polyethylene), poly(propene) (old name:
polypropylene), PVC and PTFE. It also looks briefly at how the structure of the polymers
affects their properties and uses.
Propane C3H8
Manufacture
An addition reaction is one in which two or more molecules join together to give a single
product. During the polymerisation of ethene, thousands of ethene molecules join
together to make poly(ethene) - commonly called polythene.
The number of molecules joining up is very variable, but is in the region of 2000 to 20000.
Conditions
Note: If you want the mechanism for this reaction, you can get it by following this
link to the mechanism section of the site.
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Low density poly(ethene) has quite a lot of branching along the hydrocarbon
chains, and this prevents the chains from lying tidily close to each other. Those
regions of the poly(ethene) where the chains lie close to each other and are
regularly packed are said to be crystalline. Where the chains are a random
jumble, it is said to be amorphous. Low density poly(ethene) has a significant
proportion of amorphous regions.
Note: Various sources quote estimated values for the proportion of low density
poly(ethene) which is crystalline. These vary from 50% to 75%. I have no idea what
the correct value is!
One chain is held to its neighbours in the structure by van der Waals dispersion
forces. Those attractions will be greater if the chains are close to each other. The
amorphous regions where the chains are inefficiently packed lower the
effectiveness of the van der Waals attractions and so lower the melting point and
strength of the polymer. They also lower the density of the polymer (hence: "low
density poly(ethene)").
Note: Follow this link if you don't understand van der Waals forces.
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Low density poly(ethene) is used for familiar things like plastic carrier bags and
other similar low strength and flexible sheet materials.
Manufacture
This is made under quite different conditions from low density poly(ethene).
Conditions
These catalysts work by totally different mechanisms from the high pressure
process used to make low density poly(ethene). The chains grow in a much more
controlled - much less random - way.
High density poly(ethene) has very little branching along the hydrocarbon chains -
the crystallinity is 95% or better. This better packing means that van der Waals
attractions between the chains are greater and so the plastic is stronger and has a
higher melting point. Its density is also higher because of the better packing and
smaller amount of wasted space in the structure.
Note: Despite the names, HDPE is only about 3% denser than LDPE! HDPE has a
density of about 0.95 g cm -3compared with about 0.92 for LDPE.
High density poly(ethene) is used to make things like plastic milk bottles and
similar containers, washing up bowls, plastic pipes and so on. Look for the letters
HDPE near the recycling symbol.
Poly(propene) (polypropylene): PP
Note: You should check your syllabus to find out exactly how much you need to
know. It is pointless getting bogged down in this if you don't need to! If you are
studying a UK-based syllabus and haven't got a copy of that syllabus, follow this link
to find out how to get one.
Use the BACK button (or HISTORY file or GO menu) on your browser to return to
this page later.
If your syllabus simply mentions the structure of poly(propene) with no more detail,
this is adequate.
The trick is to think about the shape of the propene in the right way:
Now line lots of them up in a row and join them together. Notice that the double
bonds are all replaced by single bonds in the process.
In a simple equation form, this is normally written as:
You have got to remember that the diagrams above are 2-dimensional. Real
poly(propene) chains are 3-dimensional. There are three different sorts of
poly(propene) depending in how the CH3 groups are arranged in space.
Isotactic poly(propene)
Note: Dotted lines show bonds going back into the screen or paper, and wedge
shapes show them coming out towards you. If you aren't very happy about the
various ways of drawing organic structures it might be worth following this link before
you go on.
This is the common form of poly(propene) which is used to make plastic crates and
ropes amongst many other things. Look for the letters PP near the recycling
symbol.
Atactic poly(propene)
In atactic poly(propene) the CH3 groups are orientated randomly along the chain.
This lack of regularity makes it impossible for the chains to lie closely together and
so the van der Waals attractions between them are weaker. Atactic poly(propene)
is much softer with a lower melting point.
Syndiotactic poly(propene)
This regularity means that the chains can pack closely, and van der Waals
attractions will be fairly strong. However, the attractions aren't as strong as in
isotactic poly(propene). This makes syndiotactic poly(propene) softer and gives it a
lower melting point.
Structure
It doesn't matter which carbon you attach the chlorine to in the original molecule.
Just be consistent on both sides of the equation.
The polymerisation process produces mainly atactic polymer molecules - with the
chlorines orientated randomly along the chain. The structure is no different from
atactic poly(propene) - just replace the CH3 groups by chlorine atoms.
Because of the way the chlorine atoms stick out from the chain at random, and
because of their large size, it is difficult for the chains to lie close together.
Poly(chloroethene) is mainly amorphous with only small areas of crystallinity.
You normally expect amorphous polymers to be more flexible than crystalline ones
because the forces of attraction between the chains tend to be weaker. However,
pure poly(chloroethene) tends to be rather hard and rigid.
These permanent dipoles add to the attractions due to the temporary dipoles which
produce the dispersion forces.
Note: If you aren't happy about the various sorts of intermolecular forces, it is
important to follow this link.
If you don't understand about electronegativity and polar bonds, then follow this one
as well.
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this page.
You may have come across this under the brand names of Teflon or Fluon.
Structure
Structurally, PTFE is just like poly(ethene) except that each hydrogen in the
structure is replaced by a fluorine atom.
The PTFE chains tend to pack well and PTFE is fairly crystalline. The chains are
rather rod-like, and can lie closely together rather like pencils in a box.
PTFE has a relatively high melting point of 327°C and is very resistant to chemical
attack. The carbon chain is so wrapped up in fluorine atoms that nothing can get at
it to react with it. This makes it useful in the chemical and food industries to coat
vessels and make them resistant to almost everything which might otherwise
corrode them.
Equally important is that PTFE has remarkable non-stick properties - which is the
basis for its most familiar uses in non-stick kitchen and garden tools. It also has a
very low coefficient of friction and is used in things like low-friction bearings.
Note: The reasons for the high melting point, the non-stick properties and the low
coefficient of friction are far more complex than most sources suggest. You will find
a detailed discussion of all this on a page about the physical properties of PTFE in
the section of questions that I can't answer to my satisfaction! This has become
increasingly more accurate over the years, and I am now fairly confident that it is as
close to the truth as I am likely to get.
If you might be asked about this in an exam, it is essential that you find out what
your examiners want by looking at past papers and mark schemes.
If you follow this link, you will need to use the BACK button on your browser to return
to this page.
If this is the first set of questions you have done, please read the introductory page before you
start. You will need to use the BACK BUTTON on your browser to come back here afterwards.
answers